Tetrabutylammonium Fluoride → HCID 44201000, compound

HRID 563227Notes

Reaction equation

[Si]([O:8][C@@H:9]([CH3:33])[C@@H:10]([NH:22][C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[C:25]([Cl:31])[C:24]=1[CH3:32])[C:11]1[S:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:14][N:15]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[Cl:31][C:25]1[C:24]([CH3:32])=[C:23]([NH:22][C@@H:10]([C:11]2[S:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:14][N:15]=2)[C@@H:9]([OH:8])[CH3:33])[CH:30]=[CH:29][C:26]=1[C:27]#[N:28]

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

HCID 670066044-((1R,2S)-2-(tert-butyldimethylsilyloxy)-1-(5-phenyl-1,3,4-thiadiazol-2-yl)propyl amino)-2-chloro-3-methylbenzonitrile

Product 1

HCID 44201000HCID 44201000, compound

Procedure

4-((1R,2S)-2-(tert-butyldimethylsilyloxy)-1-(5-phenyl-1,3,4-thiadiazol-2-yl)propyl amino)-2-chloro-3-methylbenzonitrile (425 mg, 0.85 mmol) was deprotected using tetrabutylammonium fluoride (1.0 M solution in THF, 1.7 mL, 1.7 mmol) in a procedure analogous to that used for the preparation of example 7. After column chromatography (50% EtOAc/hexanes) the title compound was isolated as a white solid (225 mg, 69%). 1H NMR (500 MHz, acetone-d6, δ in ppm) 7.94 (m, 2H), 7.51 (m, 4H), 6.81 (d, J=8.7 Hz, 1H), 5.88 (d, J=7.1 Hz, 1H), 5.13 (dd, J=3.5, 7.2 Hz, 1H), 5.02 (br s, 1H), 4.48 (m, 1H), 2.39 (s, 3H), 1.41 (d, J=6.3 Hz, 3H).

Workup

customthat used for the preparation of example 7

Sources & evidence

ORD record: ord-211e71adf7664dc3bd2f64c0944f426d
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067448B2

Reaction notes

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